EP0877732A1 - Sulfonsäureester von duftstoffen - Google Patents

Sulfonsäureester von duftstoffen

Info

Publication number
EP0877732A1
EP0877732A1 EP96940899A EP96940899A EP0877732A1 EP 0877732 A1 EP0877732 A1 EP 0877732A1 EP 96940899 A EP96940899 A EP 96940899A EP 96940899 A EP96940899 A EP 96940899A EP 0877732 A1 EP0877732 A1 EP 0877732A1
Authority
EP
European Patent Office
Prior art keywords
sulfonate
perfume
group
alcohol
perfumes
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP96940899A
Other languages
English (en)
French (fr)
Other versions
EP0877732B1 (de
Inventor
Mark Robert Sivik
Frederick Anthony Hartman
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Procter and Gamble Co
Original Assignee
Procter and Gamble Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Procter and Gamble Co filed Critical Procter and Gamble Co
Publication of EP0877732A1 publication Critical patent/EP0877732A1/de
Application granted granted Critical
Publication of EP0877732B1 publication Critical patent/EP0877732B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/73—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0007—Aliphatic compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring

Definitions

  • the present invention relates to novel sulfonates based upon alcohol perfumes
  • These sulfonate compounds are perfume alcohol de ⁇ vatives. comp ⁇ sing a radical that upon hvdrolysis forms an alcohol with a boiling point at 760 mm Hg of less than about 300 °C that is a perfume
  • these sulfonate compounds are incorporated into laundry and cleaning compositions
  • the present invention relates to novel sulfonate compounds used to provide alternative means of perfume delivery for a wide variety of consumer products
  • novel sulfonates have the general formulas of (I) and (II)
  • R and Z are independently selected from the group consisting of nonionic or anionic, substituted or unsubstituted C1-C 3 0 straight, branched or cyclic alkyl, alkenyl, alkynyl, alkylaryi or aryl group
  • Y is a radical that, upon hydrolysis of said sulfonate, forms an alcohol with a boiling point at 760 mm Hg of less than about 300 °C that is a perfume, and excluding geranyl and neryl methanesulfonates
  • the sulfonates have the general formulas (I) and (II).
  • R and Z are independently selected from the group consisting of nonionic or anionic. substituted or unsubstituted C C 0 straight, branched or cvclic alkyl, alkenyl, alkynyl, alkylaryl or aryl group, Y is a radical that, upon hydrolysis of said sulfonate. forms an alcohol with a boiling point at 760 mm Hg of less than about 300 °C that is a perfume, and excluding geranyl and neryl methanesulfonates
  • R and Z are selected from the group consisting of substituted or unsubstituted Ci - C 2 o straight, branched or cyclic alkyl, alkenyl, alkynyl, alkylaryl, aryl group or ring containing a herteroatom Y is preferably a radical that upon hydrolysis of said sulfonate forms perfume alcohol selected from the group consisting of
  • the more preferred sulfonates are the p-toluenesulfonates (tosylates), 4- bromobenzenesulfonates (brosylates), and methanesulfonates (mesylates) of these alcohols
  • the most preferred sulfonates are the tosylates, brosylates, and mesylates of ⁇ -citronellol, phenoxanol, cis-3-hexenol, and phenyl ethanol
  • Example 1 The procedure of Example 1 is repeated with the substitution of floraiol, ⁇ - citronellol, nonadyl alcohol, cyclohexyl ethanol, phenyl ethanol, isoborneol, fenchol, isocyclogeranol, ( ⁇ )-l ⁇ nalool, dihydromyrcenol, 2-phenyl-l -propanol, 2-ethylhe ⁇ anol, c ⁇ s-3-hexenol and/or 3,7-d ⁇ methyl-l-octanoi for the phenoxanol
  • Example 3 The procedure for Example 3 is repeated with the substitution of 4 bromobenzenesulfonyl chloride for p-toluenesulfonyl chloride.
  • Example 1 The procedure for Example 1 is repeated with the substitution of methanesulfonyl chloride for p-toluenesulfonyl chloride.
  • Example 1 The procedure for Example 1 is repeated with the substitution chlorosuifonylacetyl chloride for p-toluenesulfonyl chloride.
  • the present invention also relates to a composition for providing a prolonged scent signal to surfaces, comprising
  • R and Z are independently selected from the group consisting of nonionic or anionic, substituted or unsubstituted C 1 -C 30 straight, branched or cyclic alkyl, alkenyl, alkynyl, alkylaryl or aryl group
  • Y is a radical that, upon hydrolysis of said sulfonate, forms an alcohol with a boiling point at 760 mm Hg of less than about 300 °C that is a perfume, and excluding geranyl and neryl methanesulfonate
  • R and Z are selected from the group consisting of substituted or unsubstituted C ; - C 2 o straight, branched or cyclic alkyl, alkenyl, alkynyl, alkylaryl, aryl group or ring containing a herteroatom
  • Y is preferably a radical that upon hydrolysis of said sulfonate forms perfume alcohol selected from the group consisting of phenoxanol, floraiol, ⁇ -citronellol, nonadyl alcohoi, cyclohexyl ethanol, phenyl ethanol, isoborneol, fenchol, isocyclogeranol; ( ⁇ )-Iinalool, dihydromyrcenol, 2- phenyl-1 -propanol, 2-ethylhexanol, cis-3-hexenol and/or 3, 7-dimethyl-l-octanol
  • the earner and/or diluent employed in the instant compositions is a non-toxic, non-irritating substance which when mixed with the sulfonate denvatized perfume compound, promotes the deposition of said sulfonate derivatized perfume compound onto surfaces
  • the compositions of the present invention preferably comprise from about 25% to about 95%, preferably from about 50% to about 90% of a liquid earner
  • the carrier and/or diluent is p ⁇ ma ⁇ ly water due to its low cost relative availability, safety, and environmental compatibility
  • the level of water in the liquid earner is at least about 50%, preferably at least about 60%, by weight of the carrier Mixtures of water and low molecular weight, e g , ⁇ 100 g/mol, organic solvent, e g , lower alcohol such as ethanol, propanol, isopropanol or butanol are useful as the carrier liquid
  • Low molecular weight alcohols include monohydric, dihyd ⁇ c (glycol

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fats And Perfumes (AREA)
  • Detergent Compositions (AREA)
EP96940899A 1995-12-20 1996-11-26 Sulfonsäureester von duftstoffen Expired - Lifetime EP0877732B1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US08/575,418 US5710122A (en) 1995-12-20 1995-12-20 Sulfonate derivatized perfumes
US575418 1995-12-20
PCT/US1996/019019 WO1997022580A1 (en) 1995-12-20 1996-11-26 Sulfonate derivatized perfumes

Publications (2)

Publication Number Publication Date
EP0877732A1 true EP0877732A1 (de) 1998-11-18
EP0877732B1 EP0877732B1 (de) 2002-04-17

Family

ID=24300251

Family Applications (1)

Application Number Title Priority Date Filing Date
EP96940899A Expired - Lifetime EP0877732B1 (de) 1995-12-20 1996-11-26 Sulfonsäureester von duftstoffen

Country Status (12)

Country Link
US (1) US5710122A (de)
EP (1) EP0877732B1 (de)
JP (1) JP3705819B2 (de)
CN (1) CN1070848C (de)
AR (1) AR005159A1 (de)
AT (1) ATE216359T1 (de)
BR (1) BR9612056A (de)
CA (1) CA2240962A1 (de)
DE (1) DE69620798T2 (de)
DK (1) DK0877732T3 (de)
MX (1) MX9805089A (de)
WO (1) WO1997022580A1 (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7723285B2 (en) 2004-07-20 2010-05-25 Michigan Molecular Institute Beneficial agent delivery systems

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6610646B2 (en) 2000-06-01 2003-08-26 The Procter & Gamble Company Enhanced duration fragrance delivery system having a non-distorted initial fragrance impression
ES2318042T3 (es) 2001-09-06 2009-05-01 THE PROCTER & GAMBLE COMPANY Velas perfumadas.
CA2571033C (en) 2004-07-09 2010-09-21 The Procter & Gamble Company Roller for providing benefits to fabric
WO2007026331A1 (en) 2005-09-02 2007-03-08 The Procter & Gamble Company Laundry scent customization
WO2011002872A1 (en) 2009-06-30 2011-01-06 The Procter & Gamble Company Multiple use fabric conditioning composition with aminosilicone
JP5563147B2 (ja) 2010-04-01 2014-07-30 ザ プロクター アンド ギャンブル カンパニー オルガノシリコーン
EP2569408A1 (de) 2010-05-12 2013-03-20 The Procter and Gamble Company Pflegepolymere
WO2013064360A2 (en) 2011-11-03 2013-05-10 Unilever N.V. A personal cleaning composition
CN104093315B (zh) * 2011-12-06 2018-04-03 荷兰联合利华有限公司 抗微生物组合物
CN103224459A (zh) * 2013-04-13 2013-07-31 齐河县齐翔生物科技有限公司 利用地沟油生产脂肪酸甲酯磺酸盐的方法
US9365803B2 (en) 2014-07-28 2016-06-14 The Procter & Gamble Company Fabric treatment composition comprising an aminosiloxane polymer nanoemulsion
DE102019125584A1 (de) * 2019-09-24 2021-03-25 Henkel Ag & Co. Kgaa Tetraaminopyrimidin-basierte duft- und insektenabwehrmittelvorläuferverbindungen

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2035494A (en) * 1933-12-08 1936-03-31 Du Pont Perfume-emitting materials
GB1365063A (en) * 1970-07-01 1974-08-29 Bush Boake Allen Ltd Oligomeric organic titanium and zirconium compounds and solid was hing compositions comprising them
BE791813A (fr) * 1971-11-23 1973-05-23 Int Flavors & Fragrances Inc Procedes et compositions pour modifier la saveur ou le parfum d'une substance consommable
US4187251A (en) * 1976-12-16 1980-02-05 Schleppnik Alfred A Malodor counteractants
US4742044A (en) * 1987-08-19 1988-05-03 International Flavors & Fragrances Inc. Aralkoxy, alkoxy, alkadienyloxy and alkenyloxy-1,3,2-dioxaborinane derivatives and uses thereof in augmenting or enhancing the aroma of perfume compositions, perfumed articles and perfumed polymers
US5366665A (en) * 1991-07-30 1994-11-22 Lever Brothers Company, Division Of Conopco, Inc. Compositions comprising alkyl sulfooxyalkanoate compounds containing a beneficial reagent component
US5378468A (en) * 1992-09-22 1995-01-03 The Mennen Company Composition containing body activated fragrance for contacting the skin and method of use
GB9406574D0 (en) * 1994-03-31 1994-05-25 Unilever Plc Deodorant composition

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9722580A1 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7723285B2 (en) 2004-07-20 2010-05-25 Michigan Molecular Institute Beneficial agent delivery systems

Also Published As

Publication number Publication date
AR005159A1 (es) 1999-04-14
JP3705819B2 (ja) 2005-10-12
MX9805089A (es) 1998-10-31
JPH11501330A (ja) 1999-02-02
DE69620798D1 (de) 2002-05-23
ATE216359T1 (de) 2002-05-15
BR9612056A (pt) 1999-02-23
DK0877732T3 (da) 2002-07-01
US5710122A (en) 1998-01-20
CN1209118A (zh) 1999-02-24
DE69620798T2 (de) 2002-12-05
CA2240962A1 (en) 1997-06-26
WO1997022580A1 (en) 1997-06-26
CN1070848C (zh) 2001-09-12
EP0877732B1 (de) 2002-04-17

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